Three-component one-pot process to propargylic amines and related amide and sulfonamide compounds: application to the construction of 2-(aminomethyl)benzofurans and indoles |
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Authors: | Olivier Russo,Abdallah Hamze,Nathanä el Olivi,Jean-Daniel Brion,Sames Sicsic,Isabelle Berque-Bestel,Mouâ d Alami |
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Affiliation: | a Univ Paris-Sud, BioCIS UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.B. Clément F-92296 Châtenay-Malabry, France b CNRS, BioCIS UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.B. Clément F-92296 Châtenay-Malabry, France c Inserm U869, Université Victor Segalen, 146 rue léo Saignat, F-33076 Bordeaux, France |
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Abstract: | An efficient palladium-copper-catalyzed three-component assembling of propargyl halides, aryl or heteroaryl halides, and secondary amines is described. A wide variety of tertiary propargylic amines were synthesized in good to excellent yields from easily accessible starting materials. This three-component assembling was also effective when using potassium phthalimide or di-tert-butyliminodicarbonate instead of secondary amines. Consequently, it provides a quick entry to N-protected propargylic amines suitable intermediates for the synthesis of primary and secondary propargylic amines. In a similar way, related compounds including propargylic amide, carbamate and sulfonamide derivatives were efficiently obtained. This catalytic domino three-component process has been applied successfully to the construction of functionalized 2-(aminomethyl)benzo[b]furan or indole derivatives of biological interest. |
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